Hexamethyldisilazane → HCID 178483657, compound

HRID 1063644Notes

Reaction equation

HRID 1063644 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1.Cl.C[Si](C)(C)N[Si](C)(C)C.[CH:24]1[C:29]([O:30][C:31](Cl)=[O:32])=[CH:28][CH:27]=[C:26]([Cl:34])[CH:25]=1.[OH-].[Na+]>O>[Cl:34][C:26]1[CH:27]=[CH:28][C:29]([O:30][C:31]([N:2]([CH3:1])[CH2:3][CH2:4][C@H:5]2[CH2:10][CH2:9][C@H:8]([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]2)=[O:32])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 13838HexamethyldisilazaneHCID 14798Sodium HydroxideHCID 1390594-Chlorophenyl chloroformateHCID 178483656HCID 178483656, compound

Product 1

HCID 178483657HCID 178483657, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
145 °C

Procedure

1.55 g (7.00 mmol) of trans-4-(2-methylamino-ethyl)-cyclohexanecarboxylic acid·HCl were mixed with 18.4 mL (12.56 mmol, 1.8 eq) of hexamethyldisilazane and heated under reflux to 145° C. for 2.5 h. The solution was evaporated, the residue was suspended in THF and treated with 1.07 g (7.70 mmol, 1.1 eq) of 4-chlorophenylchloroformate at 0° C. and the solution was stirred at RT overnight. 10 mL of water was added at RT followed by 10 mL of 1M NaOH. Stirring was continued for 1 h at RT. The organic solvent was evaporated and the residue partitioned between n-hexane (×3)/H2O. The water phase was acidified with 1M HCl and extracted with EtOAc (3×). The organic phase was dried over Na2SO4 and evaporated to yield 1.92 g (81%) of trans-4-{2-[(4-chloro-phenoxycarbonyl)-methyl-amino]-ethyl}-cyclohexanecarboxylic acid, MS: 338 (M−H−, 1Cl).

Workup

  1. temperatureheated
  2. customThe solution was evaporated
  3. stirringStirring
  4. waitwas continued for 1 h at RT
  5. customThe organic solvent was evaporated
  6. customthe residue partitioned between n-hexane (×3)/H2O
  7. extractionextracted with EtOAc (3×)
  8. dry with materialThe organic phase was dried over Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-52c3610e69f645a1b8ec0f8368c75dd6
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

Loading…